One of most commonly applied chemical reactions between an amino acid and a reducing sugar is the Maillard reaction. The reactive carbonyl group of the sugar interacts with the nucleophilic amino group of the amino acid resulting interesting but poorly characterized odor and flavor molecules. This reaction is the basis of the flavoring industry, since the type of amino acid determines the resulting flavor. In this the process, numerous different flavor compounds are created. Although this reaction has been used since ancient times, the reaction is named after the chemist Louis-Camille Maillard who investigated it in the 1910s.1 
Related reactions are the Amadori rearrangement and the Heyns rearrangement. The Amadori rearrangement2 is an acid or base catalyzed isomerisation of the N-glycoside of an aldose or the glycosylamine to the corresponding 1-amino-1-deoxy-ketose, while during the Heyns rearrangement ketoses react with amines forming ketosylamines which further isomerise to the corresponding 2-amino-2-deoxy-aldoses. The second rearrangement was first described by Fisher3 and later further investigated by Heyns and Koch.4 The Heyns rearrangement reaction was further studied by Carson's and Heyns's labs and numerous different experiments were performed using fructose and other monosaccharides as starting materials.5 
Up to now the isolated yields of Heyns reactions have been moderate in most cases because this reaction suffers from a variety of problems such as competition between hydrolysis and rearrangement of the initial ketosylamines, epimer formation at position 2, separation problems, side reactions, further degradation entering into the Maillard reaction cascade etc. These difficulties caused the absence of synthetic application of this rearrangement reaction. Recently an improved method was published to increase the yield of the rearranged product from fructose.6 
Experiments using oligosaccharides as a starting compound for the Heyns reaction are rarely performed and, where they are performed, the process involves the isolation of labile ketosylamine. Stütz's group did valuable work using lactulose and turanose as a starting ketose for the reaction7 isolating lactosamine and nigerosamine as products.
To date, no oligosaccharides have been described in the literature having a reducing end structure of 1,2-dideoxy-1,2-diamino, although these compounds might be expected to be easily available by Heyns reaction of oligosaccharides characterized by a keto-hexose reducing end structural motif.
WO2007/104311 describes a range of novel compounds having useful functionality. An aim of certain aspects of the present invention is to provide an improved route to such compounds and novel intermediates for use in such a process.